Abstract
Multicomponent crystals containing diclofenac and acridine (1) and diclofenac and 6,9-diamino-2-ethoxyacridine (2) were synthesized and structurally characterized. The single-crystal XRD measurements showed that compound 1 crystallizes in the triclinic P-1 space group as a salt cocrystal with one acridinium cation, one diclofenac anion, and one diclofenac molecule in the asymmetric unit, whereas compound 2 crystallizes in the triclinic P-1 space group as an ethanol solvate monohydrate salt with one 6,9-diamino-2-ethoxyacridinium cation, one diclofenac anion, one ethanol molecule, and one water molecule in the asymmetric unit. In the crystals of the title compounds, diclofenac and acridines ions and solvent molecules interact via N–H⋯O, O–H⋯O, and C–H⋯O hydrogen bonds, as well as C–H⋯π and π–π interactions, and form heterotetramer bis[⋯cation⋯anion⋯] (1) or heterohexamer bis[⋯cation⋯ethanol⋯anion⋯] (2). Moreover, in the crystal of compound 1, acridine cations and diclofenac anions interact via N–H⋯O hydrogen bond, C–H⋯π and π–π interactions to produce blocks, while diclofenac molecules interact via C–Cl⋯π interactions to form columns. In the crystal of compound 2, the ethacridine cations interact via C–H⋯π and π–π interactions building blocks, while diclofenac anions interact via π–π interactions to form columns.
Highlights
Non-steroidal anti-inflammatory drugs (NSAIDs) are one of the most used group of drugs due to their broad spectrum of biological activity [1,2]
In the crystal of compound 2, the ethacridine cations interact via C–H· · · π and π–π interactions building blocks, while diclofenac anions interact via π–π interactions to form columns
The single-crystal X-ray diffraction measurements show that compound 1 crystallizes in the triclinic P-1 space group with one acridinium cation, one diclofenac anion and one diclofenac molecule in the asymmetric unit (Figure 1)
Summary
Non-steroidal anti-inflammatory drugs (NSAIDs) are one of the most used group of drugs due to their broad spectrum of biological activity [1,2] They are used, inter alia, as analgesic and anti-inflammatory drugs [3,4], can reduce the risk of some cancers [5] and are used in treating Alzheimer’s disease [6,7], as well as many other applications [8,9,10]. One non-steroidal drugs is diclofenac (IUPAC: 2-(2-(2,6-dichloroanilino)phenyl)acetic acid). It is a commonly used drug for degenerative joint disease, various inflammations, such as spondylitis, and is used after surgery and dysmenorrhea [11,12,13,14]. Diclofenac is detected in water and may adversely affect organisms and disturb ecosystem function [23,24,25,26,27]
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